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WO2018180739A1 - Composition de résine silicone comprenant des particules de polymère - Google Patents

Composition de résine silicone comprenant des particules de polymère Download PDF

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Publication number
WO2018180739A1
WO2018180739A1 PCT/JP2018/010928 JP2018010928W WO2018180739A1 WO 2018180739 A1 WO2018180739 A1 WO 2018180739A1 JP 2018010928 W JP2018010928 W JP 2018010928W WO 2018180739 A1 WO2018180739 A1 WO 2018180739A1
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WIPO (PCT)
Prior art keywords
polymer particles
silicone resin
polymer
particle
composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2018/010928
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English (en)
Japanese (ja)
Inventor
原田　良祐
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Sekisui Kasei Co Ltd
Original Assignee
Sekisui Plastics Co Ltd
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Filing date
Publication date
Application filed by Sekisui Plastics Co Ltd filed Critical Sekisui Plastics Co Ltd
Priority to JP2019509366A priority Critical patent/JP6934513B2/ja
Publication of WO2018180739A1 publication Critical patent/WO2018180739A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1806—C6-(meth)acrylate, e.g. (cyclo)hexyl (meth)acrylate or phenyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/04—Homopolymers or copolymers of esters
    • C08L33/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, which oxygen atoms are present only as part of the carboxyl radical

Definitions

  • the present invention relates to a polymer particle-containing silicone resin composition.
  • Organic electroluminescence has advantages in terms of visibility and viewing angle compared to conventional liquid crystal display (LCD), and also exhibits excellent features such as light weight, thin layer, and flexibility. Yes.
  • the organic layer including the light emitting layer has a high refractive index, there is a problem that total reflection and interference are likely to occur at the interface of the emitted light and the light extraction efficiency is low.
  • a method for solving the problem a method of increasing efficiency by providing a light scattering layer or the like in the light emitting layer has been proposed.
  • the light scattering layer a material in which organic particles such as silica or acrylic are dispersed in a binder resin such as acrylic is used.
  • the light emitting medium layer of the organic EL element is composed of an organic substance, and is easily deteriorated by the influence of moisture, oxygen, heat, etc. in the atmosphere. Therefore, a material having low hygroscopicity is desired as a material used around the organic EL element.
  • Patent Document 1 discloses a composition for sealing an organic light emitting device, which is a liquid composition at room temperature, has a curing temperature of 100 ° C. or less, and has an moisture content of 600 ppm or less.
  • An organic light-emitting device sealing composition characterized by containing a product is disclosed.
  • a silicone resin or the like has been proposed as in Patent Document 1, but the particles dispersed in the base material are useful as a light scattering agent and are easily dispersed in the silicone resin. None has been proposed so far.
  • An object of the present invention is to provide a polymer particle-containing silicone resin composition that is suitably used as an organic EL member having excellent light scattering properties and has low hygroscopicity.
  • the present invention [1] A polymer particle-containing silicone resin composition comprising polymer particles and an addition reaction curable silicone resin, wherein the polymer particles have an alkyl group or a cycloalkyl group having 4 or more carbon atoms (meta ) Polymer particles comprising cross-linked polymer particles of a polymerizable composition comprising at least one ester compound selected from the group consisting of acrylic acid esters and vinyl carboxylates, styrenic compounds, and cross-linking agents Containing silicone resin composition, and [2] Polymerization containing one or more ester compounds selected from the group consisting of (meth) acrylic acid esters having 4 or more carbon atoms or cycloalkyl groups and vinyl carboxylates, styrene compounds, and crosslinking agents
  • the present invention relates to polymer particles including crosslinked polymer particles of the composition.
  • a polymer particle-containing silicone resin composition that is suitably used as an organic EL member having excellent light scattering properties and has low hygroscopicity.
  • the polymer particle-containing silicone resin composition of the present invention (hereinafter sometimes simply referred to as “the composition of the present invention”) contains polymer particles and an addition reaction curable silicone resin.
  • composition of the present invention has excellent light scattering properties and low hygroscopicity
  • the polymer particles contained in the composition of the present invention are highly hydrophobic and difficult to adsorb moisture. Presumed.
  • the polymer particles contained in the composition of the present invention are excellent in dispersibility in the silicone resin, it is presumed that they are excellent in light diffusibility.
  • the polymer particles include cross-linked polymer particles of a polymerizable composition.
  • the polymerizable composition contains a specific ester compound, a styrenic compound, and a crosslinking agent.
  • the ester compound is a (meth) acrylic acid ester and / or vinyl carboxylate having an alkyl group or a cycloalkyl group having 4 or more carbon atoms.
  • the carbon number of the alkyl group or cycloalkyl group in the (meth) acrylic acid ester is 4 or more, preferably 5 or more, more preferably 6 from the viewpoint of obtaining particles having excellent light scattering properties and low hygroscopicity. From the viewpoint of obtaining particles with high efficiency, it is preferably 10 or less, more preferably 8 or less.
  • (meth) acrylic acid ester having an alkyl group having 4 or more carbon atoms or a cycloalkyl group examples include butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, (meth ) Pentyl acrylate, hexyl (meth) acrylate, heptyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, cycloheptyl (meth) acrylate, isobornyl (meth) acrylate, etc.
  • it is cyclohexyl methacrylate.
  • (meth) acrylic acid refers to acrylic acid or methacrylic acid.
  • vinyl carboxylate examples include vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl neodecanoate.
  • the content of the ester compound is not particularly limited, but is preferably 5 to 90% by mass, more preferably 10 to 80% by mass in the polymerizable composition. Content in the case of using 2 or more types of ester compounds refers to the total amount.
  • styrene compound examples include styrene, vinyl toluene, t-butyl styrene, ethyl vinyl benzene and the like, and styrene is preferable.
  • the content of the styrene-based compound is not particularly limited, but is preferably 5 to 90% by mass, more preferably 10 to 80% by mass in the polymerizable composition.
  • the mass ratio of the ester compound to the styrene compound is not particularly limited, but is preferably 1/45 to 45/1, more preferably 1 / 8 to 8/1.
  • the crosslinking agent is not particularly limited, but ethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, 1,4-butanediol di (meth) acrylate, 1,6-hexanediol di Multifunctional (meth) acrylates such as (meth) acrylates, 1,9-nonanediol di (meth) acrylates, allyl (meth) acrylates; aromatic divinyl compounds such as divinylbenzene, divinylnaphthalene, and derivatives thereof From the viewpoint of dispersibility, ethylene glycol dimethacrylate and divinylbenzene are preferable.
  • the content of the crosslinking agent is not particularly limited, but is preferably 1 to 50 parts by mass, more preferably 3 to 30 parts by mass with respect to 100 parts by mass of the total amount of the ester compound and the styrene compound. It is.
  • the volume average particle diameter of the crosslinked polymer particles is preferably 0.5 to 30 ⁇ m, more preferably 0.5 to 10 ⁇ m, and further preferably 0.5 to 5.0 ⁇ m, from the viewpoint of light diffusibility. is there.
  • the variation coefficient of the crosslinked polymer particles is preferably 5 to 30%, more preferably 5 to 25%, and further preferably 5 to 20% from the viewpoint of light diffusibility.
  • the volume average particle diameter and the coefficient of variation are measured by the following methods.
  • the volume average particle diameter and coefficient of variation of the crosslinked polymer particles are measured by Coulter Multisizer TM 3 (measurement device manufactured by Beckman Coulter, Inc.). Measurement shall be performed using an aperture calibrated according to the Multisizer TM 3 User's Manual published by Beckman Coulter.
  • the aperture used for measurement is appropriately selected depending on the size of the crosslinked polymer particles to be measured.
  • Current (aperture current) and Gain (gain) are appropriately set according to the size of the selected aperture. For example, when an aperture having a size of 50 ⁇ m is selected, the current (aperture current) is set to ⁇ 800 and the gain (gain) is set to 4.
  • a crosslinked polymer particle As a sample for measurement, 0.1 g of a crosslinked polymer particle was added to 10 ml of a 0.1% by weight nonionic surfactant aqueous solution with a touch mixer (manufactured by Yamato Kagaku Co., Ltd., “TOUCHMIXER MT-31”) and an ultrasonic cleaner (VEL). Dispersed using “ULTRASONICCLEANER VS-150” manufactured by Vocrea Co., Ltd., and used as a dispersion. During the measurement, the beaker is stirred gently to the extent that bubbles do not enter, and the measurement is terminated when 100,000 crosslinked polymer particles are measured.
  • the volume average particle diameter of the crosslinked polymer particles is an arithmetic average in a volume-based particle size distribution of 100,000 particles.
  • the polymer particles preferably further contain a silicone resin from the viewpoint of dispersibility in the silicone resin, and more preferably have a silicone resin layer on the surface of the crosslinked polymer particles.
  • a silicone resin from the viewpoint of dispersibility in the silicone resin, and more preferably have a silicone resin layer on the surface of the crosslinked polymer particles.
  • the silicone resin contained in the polymer particles the same silicone resin as described later can be used.
  • the content of the silicone resin is preferably 0.1 to 15% by mass, more preferably 0.5 to 10% by mass, based on the polymer particles.
  • the polymer particles having a silicone resin layer on the surface of the crosslinked polymer particles can be obtained by applying a surface treatment by a known method such as drying after applying a silicone resin to the crosslinked polymer particles.
  • the hydrophobicity index of the polymer particles is preferably 66 or more, more preferably 75 or more, from the viewpoint of dispersibility in the silicone resin.
  • the hydrophobicity index is measured by the following method.
  • a 200 ml glass beaker with a stirrer placed at the bottom 50 ml of ion-exchanged water is added and 0.2 g of polymer particles are floated on the water surface, and then the stirrer is gently rotated. Thereafter, the tip of the burette is submerged in the water in the beaker, and methanol is gradually introduced from the buret 5 minutes after the addition of the polymer particles while gently rotating the stirring bar. Methanol was introduced 1 ml at a time, and every 1 ml of methanol was stirred for 3 minutes, and 1 ml was then introduced.
  • Hydrophobicity index (%) 100 ⁇ methanol introduction amount (ml) / (amount of ion exchange water (ml) + methanol introduction amount (ml))
  • the hydrophobicity index is determined to be zero.
  • the water content of the polymer particles is preferably 0.5% or less, more preferably 0.3% or less, and even more preferably 0.1% or less.
  • the water content of the polymer particles is measured with a Karl Fischer moisture meter.
  • the refractive index of the polymer particles is preferably 1.500 to 1.570, more preferably 1.510 to 1.565, and still more preferably 1.520 to 1.560, from the viewpoint of light diffusibility. It is.
  • the refractive index is measured by a liquid immersion method. Specifically, first, polymer particles are placed on a glass slide, and a refractive liquid (cargill standard refractive liquid, Cargill standard refractive liquid, refractive index nD25 1.496 to 1.592 refractive index difference 0.002 Add several preparations in steps). Then, after thoroughly mixing the polymer particles and the refractive liquid, the outline of the particles is observed from above with an optical microscope while irradiating light from a high pressure sodium lamp NX35 (center wavelength 589 nm) manufactured by Iwasaki Electric Co., Ltd. from below. And when the outline is not visible, it is determined that the refractive index of the refractive liquid and the polymer particles are equal.
  • a refractive liquid carbgill standard refractive liquid, Cargill standard refractive liquid, refractive index nD25 1.496 to 1.592 refractive index difference 0.002 Add several preparations in steps. Then, after thoroughly mixing the polymer particles and the ref
  • the observation with an optical microscope is not particularly problematic as long as it is an observation at a magnification at which the outline of the polymer particles can be confirmed, but an observation magnification of about 500 times is appropriate for particles having a particle diameter of 5 ⁇ m.
  • the intermediate value between the two types of refractive liquid is set as the refractive index of the polymer particles. to decide. For example, when a test is performed with refractive liquids having a refractive index of 1.554 and a refractive index of 1.556, if there is no difference in the appearance of polymer particles between the two refractive liquids, an intermediate value of 1.555 between these refractive liquids is overlapped. The refractive index of the coalesced particles is determined. In the above measurement, the measurement is carried out in an environment with a test room temperature of 22 ° C. to 24 ° C.
  • the content of the polymer particles in the composition of the present invention is preferably 0.1 to 10% by mass, more preferably 0.5 to 8% by mass, and still more preferably from the viewpoint of light diffusibility. 1 to 5% by mass.
  • the method for producing the polymer particles is not particularly limited, but can be produced by methods such as seed polymerization, suspension polymerization, emulsion polymerization, and dispersion polymerization.
  • seed particles are prepared by a known method using a vinyl monomer such as methyl methacrylate, a molecular weight adjusting agent such as n-octyl mercaptan, a polymerization initiator such as potassium persulfate, and the like. be able to.
  • the seed particles are not particularly limited, but a volume average particle diameter of 0.1 to 3.0 ⁇ m is preferable, a weight average molecular weight of 5,000 to 100,000 is preferable, and a true spherical particle is preferable.
  • a silicone resin having a functional group used for an addition reaction is used.
  • the functional group include a vinyl group, an allyl group, a butenyl group, a petenyl group, and a hexenyl group, which are introduced into both ends, one end, and side chains of the molecular chain of the silicone resin.
  • the silicone resin include polydimethylsiloxane and polydiphenylsiloxane.
  • the content of the addition reaction curable silicone resin in the composition of the present invention is preferably 30 to 99% by mass, more preferably 60 to 90% by mass, and still more preferably 50% from the viewpoint of light diffusibility. ⁇ 80% by mass.
  • composition of the present invention may contain a silicone resin other than the addition reaction curable type, and examples thereof include methyl hydrogen polysiloxane and methyl hydrogen group-blocked dimethyl polysiloxane.
  • composition of the present invention can optionally contain other components.
  • other components include fillers, reaction inhibitors, flame retardants, heat resistance improvers, adhesion promoters, thixotropic agents, pigments, and plasticizers.
  • the composition of the present invention does not contain an organic solvent.
  • an organic solvent By not containing an organic solvent, the dimensional change upon curing due to volatilization of the organic solvent is small, and there is little concern about bleeding out of the remaining organic solvent even after curing.
  • the hygroscopicity of the composition of the present invention is evaluated by curing the composition of the present invention.
  • the moisture value after this cured product is allowed to stand for 24 hours in an environment of 24 ° C. and a relative humidity of 60% can be determined by measuring with a Karl Fischer moisture meter.
  • the moisture value after moisture absorption of the composition of the present invention is preferably 500 ppm or less, more preferably 450 ppm or less, and still more preferably 400 ppm or less, from the viewpoint of reducing hygroscopicity.
  • composition of the present invention can be cured under a platinum catalyst such as a complex salt of chloroplatinic acid and vinyl siloxane.
  • the optical properties of the composition of the present invention are evaluated by curing the composition of the present invention.
  • the cured product is applied in a transparent glass plate shape with a thickness of 30 ⁇ m, a glass cover is bonded thereto, and the coating layer is cured at 80 ° C., and the haze and total light transmittance of the glass plate are measured.
  • haze and total light transmittance are measured according to JIS K 7361-1 using a haze meter (manufactured by Nippon Denshoku Industries Co., Ltd., trade name “NDH4000”). ,taking measurement.
  • the haze of the composition of the present invention is preferably 80% or more, more preferably 90% or more, and further preferably 99% or more from the viewpoint of light diffusibility.
  • the total light transmittance of the composition of the present invention is preferably 75% or more, more preferably 85% or more, and further preferably 99% or more from the viewpoint of light diffusibility.
  • composition of the present invention is suitably used as an organic EL member because of its low hygroscopicity and excellent optical characteristics.
  • composition of the present invention can be produced by dispersing polymer particles in an addition reaction curable silicone resin.
  • Production Example 1 (Production of seed particles)
  • a separable flask equipped with a stirrer, a thermometer and a reflux condenser 3000 g of water as an aqueous medium, 500 g of methyl methacrylate as a monofunctional (meth) acrylic monomer, and n-octyl mercaptan as a molecular weight regulator
  • the inside of the separable flask was purged with nitrogen while stirring the contents of the separable flask, and the internal temperature of the separable flask was raised to 70 ° C.
  • Production Example 2 (Production of polymer particles)
  • 300 g of styrene, 500 g of cyclohexyl methacrylate, 200 g of ethylene glycol dimethacrylate as a crosslinking agent, and 8 g of 2,2′-azobisisobutyronitrile as a polymerization initiator Were dissolved in each other to obtain a monomer mixture.
  • the obtained monomer mixture was mixed with 1000 g of a surfactant aqueous solution obtained by dissolving 10 g of polyoxyethylene octylphenyl ether as a nonionic surfactant in 990 g of ion-exchanged water in advance, and high-speed emulsification / dispersion
  • An emulsion (trade name “Homomixer MARK II 2.5 type”, manufactured by Primix Co., Ltd.) was processed at 10000 rpm for 10 minutes to obtain an emulsion.
  • To this emulsion was added 24 g of the seed particle dispersion obtained in Production Example 1 (solid content: 3.4 g), and the mixture was stirred at 30 ° C. for 3 hours to obtain a dispersion.
  • Production Example 3 (Surface coating of polymer particles)
  • the polymer particles A obtained in Production Example 2 were surface-coated with methyl hydrogen polysiloxane.
  • 30 g of methyl hydrogen polysiloxane was dissolved in 1000 g of isopropyl alcohol.
  • the solution was uniformly applied to 500 g of polymer particles A by spraying.
  • the applied polymer particles were vacuum-dried at 70 ° C. for 24 hours to remove isopropyl alcohol, thereby obtaining polymer particles A-2 whose surface was coated with methyl hydrogen polysiloxane.
  • the obtained polymer particle A-2 had a hydrophobicity index of 81 and a water content of 0.03%.
  • Production Example 4 Polymer particles B were obtained in the same manner as in Production Example 2, except that 300 g of cyclohexyl methacrylate, 600 g of styrene, and 100 g of ethylene glycol dimethacrylate were used. The obtained polymer particles B had a volume average particle diameter of 1.5 ⁇ m and a refractive index of 1.555. Thereafter, the surface treatment was performed in the same manner as in Production Example 3 to obtain polymer particles B-2 surface-treated with methyl hydrogen polysiloxane. The obtained polymer particle C-2 had a hydrophobicity index of 82 and a moisture content of 0.05%.
  • Production Example 5 Polymer particles C were obtained in the same manner as in Production Example 2, except that 500 g of methyl methacrylate was used instead of cyclohexyl methacrylate. The obtained polymer particles C had a volume average particle diameter of 1.5 ⁇ m and a refractive index of 1.525. Thereafter, the surface treatment was performed in the same manner as in Production Example 3 to obtain polymer particles C-2 surface-treated with methyl hydrogen polysiloxane. The obtained polymer particle C-2 had a hydrophobicity index of 45 and a water content of 0.7%.
  • Polymer particles D were obtained in the same manner as in Production Example 2, except that 450 g of isobutyl methacrylate, 450 g of styrene, and 100 g of ethylene glycol dimethacrylate were used instead of cyclohexyl methacrylate.
  • the obtained polymer particles D had a volume average particle diameter of 1.5 ⁇ m and a refractive index of 1.535.
  • the surface treatment was performed in the same manner as in Production Example 3 to obtain polymer particles D-2 surface-treated with methyl hydrogen polysiloxane.
  • the obtained polymer particle D-2 had a hydrophobicity index of 72 and a water content of 0.04%.
  • Examples 1 to 3 and Comparative Examples 1 to 2 100 parts by mass of polydimethylsiloxane dried under reduced pressure at 150 ° C. for 2 hours (viscosity at 23 ° C. is 3000 mPa ⁇ s, both ends of the molecular chain blocked with dimethylvinylsiloxy groups) and 10 parts by mass of methyl hydrogen polysiloxane And 5 parts by mass of the polymer particles described in Table 1 were mixed and cured uniformly at room temperature in the presence of a complex salt of chloroplatinic acid and vinylsiloxane (about 10 ppm as platinum atoms) as a catalyst. Thus, the polymer particle-containing silicone resin compositions of Examples 1 to 3 and Comparative Examples 1 to 2 were obtained.
  • Examples 1 to 3 using polymer particles containing a (meth) acrylic acid ester having a C 4 or more alkyl group or a cycloalkyl group, a styrene compound, and a crosslinking agent as the polymerizable composition are as follows: Hygroscopicity and optical properties were good. On the other hand, Comparative Example 1 using polymer particles that do not contain a specific ester compound as the polymerizable composition has poor hygroscopicity, and Comparative Example 2 using silicone resin particles has poor optical properties. .
  • the polymer particle-containing silicone resin composition of the present invention can provide a composition suitable as an organic EL member.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne une composition de résine silicone comprenant des particules de polymère qui comprend des particules de polymère et une résine de silicone durcissable par addition. Cette composition de résine silicone comprenant des particules de polymère est caractéristique en ce que lesdites particules de polymère contiennent des particules de polymère réticulé d'une composition polymérisable qui contient : au moins une sorte de composé ester choisie dans un groupe constitué d'un ester d'acide (méth)acrylique possédant un groupe alkyle de 4 atomes de carbone ou plus ou un groupe cycloalkyle, et d'un vinyle d'acide carboxylique ; un composé à base de styrène ; et un agent de réticulation. La composition de résine silicone comprenant des particules de polymère de l'invention permet de fournir une composition appropriée en tant qu'élément électroluminescent organique.
PCT/JP2018/010928 2017-03-31 2018-03-20 Composition de résine silicone comprenant des particules de polymère Ceased WO2018180739A1 (fr)

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JP2019509366A JP6934513B2 (ja) 2017-03-31 2018-03-20 重合体粒子含有シリコーン樹脂組成物

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20240089727A (ko) 2022-02-14 2024-06-20 세키스이가세이힝코교가부시키가이샤 중합체 입자, 중합체 입자 조성물, 및 광학 필름

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JPH0711141A (ja) * 1993-06-21 1995-01-13 Nippon Paint Co Ltd 硬化性樹脂組成物
JP2001114808A (ja) * 1999-10-21 2001-04-24 Mitsubishi Rayon Co Ltd 酸基含有重合体ラテックス及びそれにより粒径肥大化されたゴムラテックス
JP2002514250A (ja) * 1997-01-15 2002-05-14 イーストマン ケミカル カンパニー 水性水素化珪素架橋性ラテックス組成物及びその製造方法
JP2009242626A (ja) * 2008-03-31 2009-10-22 Sekisui Plastics Co Ltd 架橋スチレン−（メタ）アクリル系共重合体粒子、その製造方法、人造大理石用組成物及び人造大理石
JP2010083987A (ja) * 2008-09-30 2010-04-15 Nippon Shokubai Co Ltd 有機粒子およびそれを用いた有機粒子含有組成物
JP2011068724A (ja) * 2009-09-24 2011-04-07 Shin-Etsu Chemical Co Ltd 光拡散性シリコーンゴム組成物及び成型物
JP2013100508A (ja) * 2012-12-07 2013-05-23 Nippon Shokubai Co Ltd エポキシ樹脂組成物
JP2015155532A (ja) * 2014-01-14 2015-08-27 積水化学工業株式会社 基材粒子、導電性粒子、導電材料及び接続構造体

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0711141A (ja) * 1993-06-21 1995-01-13 Nippon Paint Co Ltd 硬化性樹脂組成物
JP2002514250A (ja) * 1997-01-15 2002-05-14 イーストマン ケミカル カンパニー 水性水素化珪素架橋性ラテックス組成物及びその製造方法
JP2001114808A (ja) * 1999-10-21 2001-04-24 Mitsubishi Rayon Co Ltd 酸基含有重合体ラテックス及びそれにより粒径肥大化されたゴムラテックス
JP2009242626A (ja) * 2008-03-31 2009-10-22 Sekisui Plastics Co Ltd 架橋スチレン−（メタ）アクリル系共重合体粒子、その製造方法、人造大理石用組成物及び人造大理石
JP2010083987A (ja) * 2008-09-30 2010-04-15 Nippon Shokubai Co Ltd 有機粒子およびそれを用いた有機粒子含有組成物
JP2011068724A (ja) * 2009-09-24 2011-04-07 Shin-Etsu Chemical Co Ltd 光拡散性シリコーンゴム組成物及び成型物
JP2013100508A (ja) * 2012-12-07 2013-05-23 Nippon Shokubai Co Ltd エポキシ樹脂組成物
JP2015155532A (ja) * 2014-01-14 2015-08-27 積水化学工業株式会社 基材粒子、導電性粒子、導電材料及び接続構造体

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20240089727A (ko) 2022-02-14 2024-06-20 세키스이가세이힝코교가부시키가이샤 중합체 입자, 중합체 입자 조성물, 및 광학 필름

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